Amino acid salt containing compositions

ABSTRACT

A reagent composition for forming fatty acyl amido surfactants is provided which includes an alkali metal or alkaline earth metal salt of an amino compound; a polyol of molecular weight ranging from 76 to 300; and no more than 10% water.

CROSS-REFERENCES TO RELATED APPLICATIONS

This application is a continuation-in-part of Ser. No. 13/192,490 filedJul. 28, 2011.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The invention concerns compositions of alkali metal or alkaline earthmetal salts of amino acids in polyols and a general method for usingthese compositions in preparing fatty acyl amido based surfactants.

2. The Related Art

Fatty acyl amido salts are desirable surfactants. They have good watersolubility, good detergency and foaming properties. Most especially theyare mild to the skin. Unfortunately the amount of and extent of theirusage is limited because they are expensive to produce.

The most traditional and present commercial route to fatty acyl amidocarboxylic salts is found in U.S. Pat. No. 6,703,517 (Hattori et al.).Synthesis is achieved by reacting the amino acid with activated fattyacid derivatives, especially fatty acyl chlorides. The process requiresa mole equivalent of alkali to remove the hydrogen chloride byproduct ofthe reaction. There are evident waste disposal issues with thebyproducts and the added cost of chloride is not fully recoverable.

U.S. Pat. No. 7,439,388 B2 (Harichian et al.) describes a processwherein primary amido alcohol is oxidized to a corresponding amidocarboxylic acid in high yield. Illustrative is the conversion ofcocomonoethanolamide to N-cocoylglycine, mediated by use of a hinderednitroxide catalyst.

WO 2008/019807 A1 (Clariant International Ltd.) describes a process forpreparing acyl glycinates by oxidation of fatty acid monoethanolamidesusing a transition group metal catalyst, particularly a gold on titaniumdioxide nano-sized catalyst.

Direct esterification and interesterification are routes which also havebeen previously investigated. U.S. Patent Application Publication No.2006/0239952 A1 (Hattori) describes a reaction between a neutral aminoacid and a long chain fatty acid catalyzed by an alkaline substance suchas sodium hydroxide or potassium hydroxide. For instance, the reactionbetween glycine and lauric acid produces the acylated productslauroylglycine and lauroylglycylglycine. Significant byproducts includethe non-acylated forms such as glycylglycine and glycyldiketopiperazine,as well as unreacted glycine. The reaction is said to be highlyefficient (yield of the acylated forms) but this results because theratio of lauric acid starting material to glycine is extremely high.

GB 1 337 782 (Rohm Gmbh) describes an interesterification process forthe preparation of salts of N-acylaminocarboxylic acids. A carboxylicacid or an amide thereof is reacted with an aminocarboxylic acidcontaining at least three carbon atoms, the reaction being done in thepresence of at least a stoichiometric amount (based upon theaminocarboxylic acid) of salt-forming cations. Among the aminocarboxylicacids, only glycine was said to be unusable because the process resultedin considerable resinification. Higher homologues of glycine were said,however, to react well; these included alanine, beta-alanine, sarcosine,valine, leucine, phenyl glycine and phenyl alanine. Solvents such aswater or organic solvents such as dimethylformamide were said to benecessary.

DE 44 08 957 A1 (BASF AG) reports preparation of N-acyl aminocarboxylicacids by reaction of a suspension of solid anhydrous alkali metal saltsof aminocarboxylic acids and an appropriate carboxylic acid or ester.Catalytic amounts of strong base are added to the suspension to promotethe reaction. Illustrative is the reaction of equimolar amounts oflauric acid and anhydrous sodium sarcosine heated together molten at200° C. in the presence of a molar equivalent of sodium hydroxide.Although the yields are high, the resultant product is highly colored.

Japanese Patent Application 57/058,653 (Ota) reports a process forproducing a N-acylamino acid by reacting the corresponding amino acidwith an ester. Illustrative esters include methyl laurate, methylstearate and fatty acid glyceride esters such as triacetin, trilaurinand tristearin. Although a solvent was said not always to be necessary,all the examples utilize polar solvents such as acetonitrile, dimethylsulfoxide or N,N-dimethylformamide.

None of the known esterification or interesterification processes arewithout a disadvantage. Many require relatively high temperatures and/orstrong alkali to progress the reaction. These conditions promote sidereactions of the amino acids with themselves rather than with the fattyacylating reagent. These competing reactions squander expensive aminoacid starting reagent and require removal cleanup steps. Yields are alsoadversely affected. Furthermore, the necessary conditions for reactionin the known art are too harsh for the simpler amino acids.

In the present commercial routes to fatty acyl amido carboxylic saltssuch as cocoyl glycinate, the sodium glycine reactant ordinarily is acirca 20% active in a water slurry. Reaction of acyl halide with theaqueous slurry of sodium glycine is subject to several problems. Rate ofaddition must be carefully controlled to avoid overheating the reactionwhich leads to splattering and safety issues. A better form ofdelivering alkali metal glycine, and indeed all types of metal aminoacids, to acyl halide reactions would be a significant advance.

SUMMARY OF THE INVENTION

A reagent composition is provided for forming fatty acyl amidosurfactants which includes:

-   -   (i) from 1 to 90% by weight of an alkali metal or alkaline earth        metal salt of an amino compound, the compound having a        structure (I) which is

-   -    wherein R² is hydrogen, CH₂COOX or a C₁-C₅ alkyl radical; R³ is        hydrogen; R⁴ is selected from the group consisting of        (CH₂)_(m)CO₂X, (CH₂)_(m)SO₃X, CH₂NR²(CH₂)_(m)OH and glucosyl        radicals; R⁵ is selected from the group consisting of hydrogen,        hydroxyphenyl, C₁-C₆ hydroxyalkyl, C₁-C₁₀ alkyl, benzyl,        hydroxybenzyl, alkylcarbamido, thioalkyl, and carboxylic        radicals; X is an alkali or alkaline earth metal cation; and m        ranges from 0 to 6; and    -   (ii) from 10 to 99% by weight of a polyol of molecular weight        ranging from 76 to 300; and    -   (iii) from 0 to 10% by weight of water.

DETAILED DESCRIPTION OF THE INVENTION

Now we have found that a substantially anhydrous composition of analkali metal or alkaline earth metal amino compound (e.g. glycine)delivered through a polyol medium is an excellent reagent composition.In combination with fatty acid esters, the reagent composition can reactto form fatty amido surfactants.

Advantageously, the reagent composition and also any reaction medium inwhich it is employed may be substantially free of water. Bysubstantially free of water is meant amounts from 0 to 10%, preferablyfrom 0 to 5%, more preferably from 0 to 3%, still more preferably from 0to 1%, and especially from 0.05 to 1% by weight of water. Water ofhydration (such as found associated with the amino carboxylic orsulphonic acid monohydrate) is not considered to count as part of waterpresent in the reagent composition and/or any reaction medium.

Reaction mixtures for producing fatty acyl amido surfactants desirablyshould have a pKa at 25° C. ranging from 9.5 to 13, and preferably from10.5 to 11.5.

The preferred alkali metal or alkaline earth metal salts are sodium,potassium, calcium and magnesium. The salt of the amino compound mayeither be in an anhydrous or hydrated form.

Suitable amino compounds are those selected from the group consisting ofalanine, valine, leucine, isoleucine, phenylalanine, tryptophan,methionine, proline, aspartic acid, glutamine acid, glycine, serine,threonine, cysteine, tyrosine, asparagines, glutamine, lysine, arginine,histidine, sarcosine, n-methylglucamine, glucamine and taurine.Particularly preferred are glycine, sarcosine, taurine,N-methylglucamine and glucamine.

The term “fatty acid” is herein defined as an 8 to 22 carbon carboxylicradical containing material that may be saturated, unsaturated,branched, unbranched or a combination thereof.

A variety of fatty acid esters may be suitable as co-reactant with thereagent composition. Most preferable as co-reactant are the C₁-C₃ alkylesters of a C₈-C₂₂ fatty acid. Illustrative are methyllaurate,methyloleate, methylinoleate, methylmyristate, methylstearate,methylpalmitate, ethyllaurate, ethyloleate, ethyllinoleate,ethylmyristate, ethylstearate, ethylpalmitate, n-propyllaurate,n-propyloleate, n-propyllinoleate, isopropyllaurate, isopropyloleate,isopropyllinoleate, isopropylmyristate, isopropylstearate,isopropylpalmitate and mixtures thereof. Particularly suitable is methylcocoate.

The C₁-C₃ alkyl esters of C₈-C₂₂ fatty acids may be generated fromtriglycerides by hydrolysis with a respective C₁-C₃ alkanol. Mostsuitable as the alkanol is methanol. Amongst useful but not exclusivetriglycerides are coconut oil, corn oil, palm kernel oil, palm oil,soybean oil, sunflowerseed oil, cottonseed oil, rapeseed oil, canolaoil, castor oil and mixtures thereof. Most preferred is coconut oil.

An alternative fatty acid ester suitable as a co-reactant in the processare the glyceride esters. These glycerides may be selected frommonoglycerides, diglycerides, triglycerides and mixtures thereof.Illustrative monoglycerides are monoglyceryl laurate, monoglyceryloleate, monoglyceryl linoleate, monoglyceryl myristate, monoglycerylstearate, monoglyceryl palmitate, monoglyceryl cocoate and mixturesthereof. Illustrative diglycerides include glyceryl dilaurate, glyceryldioleate, glyceryl dilinoleate, glyceryl dimyristate, glyceryldistearate, glyceryl diisostearate, glyceryl dipalmitate, glycerylcocoate, glyceryl monolaurate monomyristate, glyceryl monolauratemonopalmitate and mixtures thereof. Illustrative but non-limitingtriglycerides include oils and fats such as coconut oil, corn oil, palmkernel oil, palm oil, soybean oil, cottonseed oil, rapeseed oil, canolaoil, sunflowerseed oil, sesame oil, rice oil, olive oil, tallow, castoroil and mixtures thereof. Most preferred is coconut oil. Use of mono-,di- and tri-glycerides as the co-reactant has an advantage over theC₁-C₃ alkyl esters of C₈-C₂₂ fatty acids. The latter are generally madefrom breakdown of triglycerides. Conversion from the triglycerides addsan extra step to the process. A disadvantage of using the mono-, di- andtri-glycerides as starting co-reactant is the albeit good but slightlylower yields of resultant acyl glycinate product.

Schematically the process of preparing C₈-C₂₂ acyl amido carboxylic orsulphonic acids salts thereof from the reaction of the reagentcomposition with a C₁-C₃ alkyl ester of a C₈-C₂₂ fatty acid (hereinafterthe “monoester route”) corresponds to the following reaction scheme(which optionally includes a triglyceride precursor for illustrativepurposes).

wherein R is a C₇-C₂₁ saturated or unsaturated alkyl radical; R¹ is aC₁-C₄ alkyl; R² is hydrogen, CH₂COOX or a C₁-C₅ alkyl radical; R³ ishydrogen; R⁴ is selected from the group consisting of (CH₂)_(m)CO₂X,(CH₂)_(m)SO₃X, CH₂NR²(CH₂)_(m)OH and glucosyl radicals; R⁵ is selectedfrom the group consisting of hydrogen, hydroxyphenyl, C₁-C₆hydroxyalkyl, C₁-C₁₀ alkyl, benzyl, hydroxybenzyl, alkylcarbamido,thioalkyl, and carboxylic radicals; X is an alkali or alkaline earthmetal cation; and m ranges from 0 to 6.

Schematically the process of preparing C₈-C₂₂ acyl amido carboxylic orsulphonic acids or salts thereof directly with a triglyceride as aco-reactant corresponds to the following reaction scheme.

wherein R is a C₇-C₂₁ saturated or unsaturated alkyl radical; R″ and R′″independently are selected from C₇-C₂₁ radicals which may be the same ordifferent, hydrogen and mixtures thereof; R² is hydrogen, CH₂COOX or aC₁-C₅ alkyl radical; R³ is hydrogen; R⁴ is selected from the groupconsisting of (CH₂)_(m)CO₂X, (CH₂)_(m)SO₃X, CH₂NR²(CH₂)_(m)OH andglucosyl radicals; R⁵ is selected from the group consisting of hydrogen,hydroxyphenyl, hydroxyalkyl, C₁-C₁₀ alkyl, benzyl, hydroxybenzyl,alkylcarbamido, thioalkyl, and carboxylic radicals; X is an alkali oralkaline metal cation; and m ranges from 0 to 6.

Salts of the amido carboxylic or sulphonic acid products of the processpreferably are selected from sodium, potassium or mixed cations.Particularly suitable as the R¹ group is a methyl radical.

An advantage of the present reagent composition and use in forming fattyacyl amido surfactants relative to wet reagents in the traditionalSchotten-Bauman acyl halide route is that unsaturated fatty esters suchas oleyl and linoleyl esters can be tolerated. These unsaturated acidswill not undergo decomposition or generate color bodies as happens inthose reactions of the known art. Minimum byproducts are produced in theprocess. For instance, where a sodium glycine reagent composition is thereactant, we have found no evidence of a glycyiglycine orglycyldiketopiperazine. Neither are there any waste streams. As isevidenced from the reaction schematic above, when glycerol is thepolyol, the glycerol liberated from the triglyceride can be utilized asa reaction medium. The alcohol (for instance methanol) that distills offfrom the main reaction can be fed back into the triglyceride hydrolysisreaction to form new methyl fatty acid ester.

Relative molar amounts of amino compound or salt thereof to fatty acidester may range from about 3:1 to about 1:3, preferably from about 2:1to about 1:1, more preferably from 1.3:1 to 1.05:1.

Polyols of molecular weight ranging from 76 to 300, preferably from 90to 200, will form part of the reagent composition and may also serve asa medium for subsequent reactions with fatty acid esters. The relativemole ratio of polyol to the amino compound may range from about 8:1 toabout 1:1, preferably from about 6:1 to about 1:1, and more preferablyfrom about 2:1 to 1:1.

Most preferred as the polyol are glycerol, propylene glycol and mixturesthereof. Generally, the total amount of polyol will range from 10 to99%, preferably 30 to 85%, and optimally 50 to 75% by weight of thereagent composition.

When the reagent composition is used in a process to prepare fatty acylamido compounds, temperature conditions for the reaction may range fromabout 50° C. to about 150° C., preferably from about 80° C. to about140° C., and optimally from about 110° C. to about 130° C.

Basic metal salt containing catalysts are usefully present to improvereaction speeds and conversion levels. Particularly useful are alkalineand alkaline earth metal containing hydroxides, phosphates, sulphatesand oxides including calcium oxide, magnesium oxide, barium oxide,sodium oxide, potassium oxide, calcium hydroxide, magnesium hydroxide,calcium phosphate, magnesium phosphate and mixtures thereof. Mostsuitable are calcium oxide and magnesium oxide, with the former beingpreferred. Amounts of the basic metal salt catalyst may range from about1 to about 20%, preferably from about 1 to about 10%, more preferablyfrom about 1.5 to 5% by weight of starting amino compound present in thereaction.

Buffering compounds may also in some embodiments have utility to improveconversions and reaction times. Suitable buffers include trisodiumphosphate, disodium hydrogen phosphate, sodium citrate, sodiumcarbonate, sodium bicarbonate, sodium borate and mixtures thereof.Particularly useful is trisodium phosphate. Amounts of the buffer mayrange from about 1 to about 30% by weight of the amino compound or saltthereof present in the reaction. Preferably the amount is from about 5%to about 15% by weight of the starting amino compound or salt thereofpresent in the reaction.

Advantageously, distillation of the alkanol (e.g. methanol) in themonoester route can be done under atmospheric as well as reducedpressure conditions.

The reaction products for many purposes need not be isolated. Forinstance, polyol may not need to be separated where the fatty acyl amidocompounds are intended for personal care products such as body washes,toilet bars, shampoos or even lotions. Some polyols, particularlyglycerol and propylene glycol are useful in these products as amoisturizer. In circumstances where glycerol or propylene glycol,unreacted starting materials or the minor byproducts are undesirable,the resultant reaction mixture can be further processed. For instance,the mixture can be treated with ethanol which precipitates out the acylamido carboxylic or sulphonic salt or with acidification the free acidform but retains polyol and unreacted starting materials solubilizedwithin the ethanol. Upon separation of the acyl amido carboxylic orsulphonic acid/salt product, the unreacted starting materials and polyolcan be recycled for further reaction by evaporation (e.g. distillation)of the ethanol.

Colored byproducts ordinarily generated in previously known routes tofatty acyl amido carboxylic or sulphonic salts are avoided through thedescribed process. Confirmation of the absence of colored species, forinstance where glycine is a reactant, any glycyiglycine andglycyldiketopiperazine has been established as not present throughchromatography and/or mass spectroscopy analytical procedures. Yet,perhaps the best indicator of the clean nature of products formed in theprocess is the visual lack of dark coloration (e.g. absence of tan,brown, or even green/blue heretofore evident from other glycinateforming pathways). Subsequent to heating, the hot liquid mass ofreaction product bearing fatty acyl amido carboxylic or sulphonicacid/salt product and polyol is removed from the reactor and forms asemi-solid. Color of this mass is evaluated by the Hunter Lab ColorScale. The resultant mass from the reaction can vary in color from whiteto slightly off-white. On the Hunter scale, the key parameter will bethe L value which is a reflectance measure of brightness. L should rangebetween 70 and 100, preferably from 75 to 100, optimally from 90 to 100.Desirably, the b value can also be considered. The “b” may range from 0to 20, preferably from 0 to 15 and optimally from 0 to 3. Of less impactis the “a” value, which may range from −2 to 8, preferably −1 to 5, andoptimally from 0 to 4. Values for the present invention were establishedby comparing the reaction resultant mass color (at the end of theprocess) with a Color Metric Converter available online athttp://www.colorpro.com/info/tools/convert.htm.

All documents referred to herein, including all patents, patentapplications, and printed publications, are hereby incorporated byreference in their entirety in this disclosure.

The term “comprising” is meant not to be limiting to any subsequentlystated elements but rather to encompass non-specified elements of majoror minor functional importance. In other words the listed steps,elements or options need not be exhaustive. Whenever the words“including” or “having” are used, these terms are meant to be equivalentto “comprising” as defined above.

Except in the operating and comparative examples, or where otherwiseexplicitly indicated, all numbers in this description indicating amountsof material ought to be understood as modified by the word “about”.

It should be noted that in specifying any range of concentration oramount, any particular upper concentration can be associated with anyparticular lower concentration or amount.

The following examples will more fully illustrate the embodiments ofthis invention. All parts, percentages and proportions referred toherein and in the appended claims are by weight unless otherwiseillustrated.

EXAMPLE 1

Synthesis of Sodium Glycinate Reagent Composition

A glass reactor vessel was charged with 25 g glycerol, 13.5 g of glycineand 7.0 g of sodium hydroxide pellets. These were heated together at120° C. for one hour. Water was continuously distilled from theresultant reagent composition. This reagent composition provided a 100%yield of sodium glycine in glycerol. This composition can be prepared asa pre-mix as herein described and then charged to a reactor with a fattyacid ester to conduct a reaction to produce cocoyl glycinate.Alternatively, the sodium glycine slurry and glycerol can be formed insitu as is described in the following reaction scheme.

Cocoyl Glycinate Via Monoester Route

A 250 ml 3-neck glass reactor vessel was used to conduct a series ofcomparative experiments. A central neck was fitted with a stirring rodwith Teflon® blade at one end and a motor for rotating the rod at asecond end. A second neck of the reactor was fitted with a water-cooledcondenser leading to a Dean-Stark trap for collecting methanol generatedin the interesterification reaction. The third neck was fitted with athermometer attached to a temperature control device. The reactor wasexternally heated in a glas-col heating mantle. In experiment 1, thereactor was charged with 25 g glycerol, 0.41 g calcium oxide, 17.5 gsodium glycine, and 39 g cocoyl methyl ester. Initially two phases werepresent in the reactor. The reactants were then heated at 120° C. for 2hours under constant stirring and dry nitrogen. The reactor contentswere then cooled to a point just above solidification and removed fromthe reactor. The resultant mass was a white colored paste. Analysis byliquid chromatography revealed an approximately 87% yield (based onstarting glycine) of sodium cocoyl glycinate.

The resultant mass contained 50.3% sodium cocoyl glycinate, 7.2% C₈-C₁₈fatty acids, 34.1% glycerol, 1.6% glycine, less than 1.0% methylcocoate, and the remainder calcium oxide and other minor materials.

Via liquid chromatography/mass spec analysis, the sodium cocoylglycinate was shown to contain the following fatty acid chain lengthdistribution based on % amounts in the total resultant mass: 5.0% C₈,3.8% C₁₀, 27.4% C₁₂, 9.7% C₁₄, 4.5% C₁₆ and 6.9% C₁₈. The C₁₈ glycinatewas a mixture of stearic, oleic and linoleic isomers. The unsaturatedC₁₈ compounds survived the reaction conditions in contrast to theirabsence under conditions of the alternate acyl chloride route.

A series of further experiments were conducted to evaluate theimportance of catalyst, buffer, reaction times and temperatures. Theseexperiments are recorded in Table I. Reactants and conditions areidentical to experiment 1, except where otherwise indicated throughfootnotes for Table I.

TABLE I Reaction Reaction Hunter Lab Experiment Calcium Mixture TimeYield Temp. Color Scale No. Glycerol Oxide Buffer pKa (Hours) (%) (° C.)L a b 1 Yes Yes None 9.6 2 87 120 95.28 0.56 12.98 2 Yes Yes Yes¹ 9.6 2 95+ 120 93.12 −0.52 2.41 3 Yes Yes² None 9.6 2  95+ 120 93.12 −0.522.41 4 Yes None None 9.6 4-5 40-50 120-140 95.28 0.56 12.98 5 None NoneNone 9.6 5 <10  110-150 46.2 9.21 33.05 6 None Yes None 9.6 2 <5 12046.2 9.21 33.05 7 None Yes Yes 9.6 2 <5 120 46.2 9.21 33.05 8 Yes Yes³Yes 9.6 2 75 120 93.12 −0.52 2.41 9 Yes Yes⁴ Yes 9.6 2 30-50 110-12093.53 −0.12 6.07 10 Yes Yes None 10.2 5 84 120 93.12 −0.52 2.41 11 YesYes Yes⁶ 8.9 5 94 120 93.12 −0.52 2.41 12 Yes Yes Yes 9.74 2 89 12093.12 −0.52 2.41 13 Yes Yes Yes 7.6 2  0 120 68.93 12.44 36.72 14 YesYes Yes 7.7 2  0 120 69.00 12.50 37.00 15 Yes Yes Yes 8.9 2  0 120 69.1012.60 37.01 ¹Trisodium phosphate at 1.5 g.; ²Doubled CaO to 0.82 g.;³Magnesium oxide substitute for calcium oxide at 0.41 g. ⁴Zinc oxidereplacement for calcium oxide at 0.41 g.; ⁵Propylene glycol replacedglycerol at 25 g.; ⁶Trisodium phosphate doubled to 3.0 g.

Experiment 4 in Table I demonstrates that in the absence of calciumoxide yields are reduced to a range of 40-50%. Experiment 5 demonstratesthat in the absence of glycerol, hardly any sodium cocoyl glycinate isformed. Similar results are seen in experiments 6 and 7 where onlycatalyst is present to influence the reaction. From these experiments itis clear that the medium is the crucial aspect in driving goodconversions. Glycerol is best and propylene glycol is second best butalso useful.

Experiments 13-15 demonstrate that reactions run at a pKa substantiallylower than 9.5 do not result in any glycinate product. Zero yields werenoted at pKa of 7.6, 7.7 and 8.9.

EXAMPLE 2

A series of different reaction mediums were evaluated. The experimentswere conducted with reactants and conditions identical to experiment 1,except where otherwise indicated as footnotes to Table II.

TABLE II Reaction Reaction Hunter Lab Experiment Calcium Mixture TimeTemp. Yield Color Scale No. Medium⁷ Oxide Buffer pKa (Hours) (° C.) (%)L a b 16 Methanol Yes⁸ None 9.6 2 120 <5 93.39 2.01 24.30 17 Ethanol YesYes 9.6 4-5 80 <5 93.39 2.01 24.30 18 Isopropyl Yes Yes 9.6 5 90 <593.39 2.01 24.30 Alcohol 19 Toluene None None 9.6 5 110 <5 93.39 24.3020 Isoamyl None Yes⁹ 9.6 5 120 <5 93.39 2.01 24.30 Alcohol 21 Water YesNone 9.6 3 100 <5 68.93 12.44 36.72 ⁷Amount of the medium was 100 g.⁸Doubled CaO to 0.82 g. ⁹Trisodium phosphate doubled to 3.0 g.

Based on the results reported in Table II, it is evident that methanol,ethanol, isopropyl alcohol, toluene and isoamyl alcohol were ineffectivein providing any reasonable conversion of reactants into sodium cocoylglycinate. Only glycerol, and to a slightly lesser extent, propyleneglycol were effective at driving the reactions to high conversions.

EXAMPLE 3

A set of experiments were conducted to evaluate whether amino acidsother then glycine, amino sulphonic acids, and glucosyl amines wouldalso be reactive in the process. The experiments were conducted withreactants and conditions identical to Experiment 1, except glycine wasreplaced by sarcosine, taurine or N-methylglucamine. Any further changesare indicated as footnotes to Table III.

TABLE III Reaction Reaction Hunter Lab Experiment Amino Calcium MixtureTime Yield Temp. Color Scale No. Reactant Glycerol Oxide Buffer pKa(Hours) (%) (° C.) L a b 22 Sarcosine Yes Yes Yes 9.6 2 55-65 120 76.755.24 53.64 23 Taurine Yes Yes Yes¹ 9.7 2  95+ 120 93.3 −0.12 6.07 24N-methylglucamine Yes Yes Yes 9.6 2 92 120 92.14 4.4 32.75 ¹Trisodiumphosphate at 1.5 g.

Experiments 22 and 23 produced respectively good yields of sodiumcocoylsarcosinate and sodium cocoyltaurate. Amides of N-methyl glucaminewere also provided in good yields as detailed in Experiment 24.

EXAMPLE 4

Cocoyl Glycinate Via Triqlycerides

A 250 ml 3-neck glass reactor vessel was used to conduct a series ofcomparative experiments. A central neck was fitted with a stirring rodwith Teflon® blade at one end and a motor for rotating the rod at asecond end. A second neck of the reactor was fitted with a water-cooledcondenser leading to a Dean-Stark trap for collecting distillatesgenerated in the interesterification reaction. The third neck was fittedwith a thermometer attached to a temperature control device. The reactorwas externally heated in a glas-col heating mantle. In experiment 1, thereactor was charged with 25 g glycerol, 17.5 g Na glycine, 0.41 gcalcium oxide, 3 g sodium phosphate (buffer), and 41.2 g coconut oil.Initially two phases were present in the reactor. The reactants werethen heated at 130° C. for 2 hours under constant stirring. The reactorcontents were then cooled to a point just above solidification andremoved from the reactor. The resultant mass was a white colored paste.

Analysis by liquid chromatography revealed an approximately 92.7% yield(based on starting glycine) of sodium cocoyl glycinate. This experimentis identified as number 25 in Table IV. Experiments 26-28 were done withreactants and under conditions identical to experiment 25, except whereotherwise noted in the Table.

TABLE IV Reaction Reaction Hunter Lab Experiment Calcium Mixture TimeYield Temp. Color Scale No. Glycerol Oxide Buffer Triglyceride pKa(Hours) (%) (° C.) L a b 25 Yes Yes Yes Coconut Oil 9.6 2 92.7 130 95.200.56 12.98 26 Yes Yes Yes Coconut Oil 9.6 5 72 120 95.06 −0.27 11.98 27Yes Yes None Coconut Oil 9.6 5 91.8 120-130 93.53 −0.12 6.07 28 Yes YesYes Corn Oil 9.6 5 60 120 90.10 1.34 39.74

EXAMPLE 5

A number of experiments were conducted to evaluate different forms ofsodium glycine reagent compositions. The amounts of material in each ofthe experiments and their type are identical to that of Experiment 1under Example 1. These further experiments are reported under Table V.

TABLE V Reagent Water Reaction Hunter Lab Experiment Calcium AminoRemoval Time Yield Temp. Color Scale No. Glycerol Oxide Buffer BaseCompound In situ pKa (Hours) (%) (° C.) L a b 29 Yes Yes Yes NaOHGlycine Yes (1 hr) 9.6 4 92 120 92.94 0.84 31.66 30 Yes Yes Yes NaOHGlycine No 9.6 4 74 120 94.51 −0.42 14.23 31 Yes Yes Yes KOH Glycine Yes(1 hr) 9.6 4 80 120 92.94 0.84 31.8 32 Yes Yes No NaOH Sarcosine Yes (1hr) 10 4 55 120 76.9 5.2 53.6 33 Yes Yes No NaOH Taurine Yes (1 hr) 9.54 90 140 95.6 −0.75 9.47

While the invention has been described in detail with reference tospecific embodiments thereof, it will be apparent to one skilled in theart that various changes and modifications can be made therein withoutdeparting from the spirit and scope thereof.

What is claimed is:
 1. A process for forming fatty acyl amidosurfactants that comprises: (i) reacting from 1 to 90% by weight of analkali metal or alkaline earth metal salt of an amino compound, thecompound having a structure (I) which is

wherein R₂ is hydrogen, CH₂COOX or a C₁-C₅ alkyl radical; R³ ishydrogen; R⁴ is selected from the group consisting of (CH₂)_(m)CO₂X,(CH₂)_(m)SO₃X, CH₂NR₂(CH2)_(m)OH and glucosyl radicals; R₅ is selectedfrom the group consisting of hydrogen, hydroxyphenyl, C₁-C₆hydroxyalkyl, C₁-C₁₀ alkyl, benzyl, hydroxybenzyl, alkylcarbamido,thioalkyl, and carboxylic radicals; X is an alkali or alkaline earthmetal cation; and m ranges from 0 to 6; and (a) from 10 to 99% by weightof a polyol of molecular weight ranging from 76 to 300; and (b) from 0to 10% by weight of water, and (c) a basic salt containing catalystselected form the group consisting of alkaline earth comprising metalcontaining hydroxide, phosphates, sulphates and oxides, wherein theoxides are selected from the group consisting of calcium oxide,magnesium oxide, barium oxide, sodium oxide, potassium oxide; (ii)heating reactants from step (i) to form acyl amido compounds having astructure (II)

wherein R is C₇-C₂₁ saturated or unsaturated alkyl radical provided bythe fatty acid ester; and the resultant mass has a Hunter Lab Coir Scalevalue ranging from 70 to 100; and (iii) recovering a resultant mass fromthe process.
 2. The process according to claim 1 wherein the polyol isglycerol or propylene glycol.
 3. The process according to claim 1wherein the alkali metal or alkaline earth metals are selected from thegroup consisting of sodium, potassium, calcium, magnesium and mixturesthereof.
 4. The process according to claim 1 wherein the amino compoundis selected from the group consisting of alanine, valine, leucine,isoleucine, phenylalanine, tryptophan, methionine, proline, asparlicacid, glutamine acid, glycine, serine, threonine, cysteine, tyrosine,asparagines, glutamine, lysine, arginine, histidine, sarcosine,n-methylglucamine, glucamine and taurine.
 5. The process according toclaim 1 wherein the amino compound is selected from the group consistingof glycine, sarcosine and taurine.
 6. The process according to claim 1wherein the alkali metal or alkaline earth metal salt of the aminocompound is sodium glycine.
 7. The process according to claim 1 whereinwater ranges from 0.05 to 1% water.